To me, the best music of the Grateful Dead ranks as one of the greatest achievements of human life on this planet. It has taken DNA millions of years to evolve to the point where it could unleash the awesome magnificence of Grateful Dead space music onto the quivering masses of protoplasm

–Anonymous message to the band offered in response to a 1987 poll conducted by the Grateful Dead fan magazine The Golden Road

The glory and the dilemma of the greatest band in American history is that everyone has their own Grateful Dead. Mine started with a Maxell XLII cassette tape lent to me by Dave the Bike Tech at summer camp in 1994. I was 12. A year later, I saw the Dead for the first time, a sloppy show in St. Louis. It was also the last time – a month or so after that concert, Jerry Garcia, the band's legendary lead guitarist, died in rehab. By then I was back at summer camp, and Dave the Bike Tech broke the news. Most of the counsellors at the camp were Deadheads, too. We sat around in a circle, did a little drumming, cried a bit. I wore a black armband and lied about having attended the band's final two performances, at Soldier Field in Chicago, so that the counsellors who had ducked down from Minnesota for the last stand would think I was cool. They've been my favourite band ever since.

But that's just me. If you're a fan, you have your own Grateful Dead. Part of the pleasure of loving them is encountering your fellow travellers in all sorts of places – especially this year, when everyone seems to be enjoying the trip. 2015 marks 50 years since the band formed in Northern California, and 20 years since those last shows in Chicago. To celebrate, the surviving members of the Dead are reuniting next month for a final run of concerts at the very same Soldier Field, which they insist will be the last time they'll perform together.

Naturally, this moment of possibility and profit has been embraced by publishers, who are unleashing a slew of new books about the Dead. They range from generic narratives to oral histories to memoirs to academic chronicles, and they exacerbate the fundamental Deadhead dilemma: if everyone has their own Grateful Dead, how do you write a meaningful book about them?

If you're Peter Richardson, a Bay Area professor best known for his book A Bomb in Every Issue, a history of the American leftist magazine Ramparts, you try to approach the band through the lens of the academy. No Simple Highway seeks to position the group in "the broader sweep of American cultural history." His argument is that the Dead embody a particularly American yearning for utopian possibility, which he traces through band's commitment to ideals of ecstasy (the feeling, not the drug), mobility (their frontier-inspired Western identity) and community ("from the outset, the Dead's enterprise was tribal as well as utopian").

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No Simple Highway alternates between a reconstruction of the Dead story, based largely on extant accounts, interviews and old newspaper clippings, and bursts of relevant history and historiography. The result is disjointed, with jarring transitions between a good yarn and heavy-handed connection making. Despite that, it's a pleasant-enough read, if bloodless: Richardson admits to having not been a fan of the band until he realized that their work intersected with his academic interests. The book closes with his account of trying to catch some surviving members of the Dead on stage in their various post-Garcia incarnations, ending in a cringe-inducing description of dropping acid at a concert in Berkeley. You feel bad for him because of the Live Your Boomer Dream Day quality of it, but also because of all the years he spent not listening to the Grateful Dead.

The book is at its best when analyzing the words that made the Dead's songs, in particular the writing of Robert Hunter, whose vaguely mythical lyrics, which say a lot without really saying anything at all, are an essential part of what makes the Dead the Dead. Richardson offers elegant stretches of literary criticism, exploring the tension between the abusive domestic situations of Hunter tunes such as Brown-Eyed Woman and the Dr. Spock-fuelled parenting anxiety of the 1970s. His sophisticated close reading of Touch of Grey, the group's surprise smash 1987 hit, made me understand a song I've heard hundreds of times in new, nuanced ways.

But the book is too often hampered by its argument for the band's broader cultural position, culminating in situating the Dead as a belaboured foil for Ronald Reagan's ascent. Ultimately, No Simple Highway can't escape the kind of boring anchor of its own stated mission: "While many of their peers flashed brilliantly across the American scene, the Grateful Dead became one of the counterculture's most distinctive and durable institutions," Richardson writes in his introduction. "This book raises a deceptively simple question: why?"

That's not a question that interests Bill Kreutzmann, one of the Dead's two drummers and a founding member of the group. His new memoir, Deal, is a hell of a lot more fun than Richardson's book. Perhaps not coincidentally, it's also much less concerned with arriving at any sort of certainty. "I could speculate on how something in the music that we made hints at some kind of timeless truth," Kreutzmann writes, "and perhaps even captures the underlying eternal spirit of the American people…the truth is, nobody knows how or why we've had the staying power." (His co-author, Benjy Eisen, puts it more succinctly in his introduction: "Nobody knows why it endures so persistently, although plenty of other books have attempted to answer that question. This book doesn't even attempt to ask it.")

Deal's profound uninquisitiveness is its greatest strength. It's shallow but juicy, the sort of book that arrives accompanied by packs of publisher-produced promotional rolling papers. Narrated by a rambling Kreutzmann in avuncular stoner mode, it's a haphazard history packed with endless stories and pleasantly little insight. Reading it is like talking to someone a touch under the influence: unpredictable, funny, repetitive, petty. It's a mess, but a fun one.

Deal echoes No Simple Highway in its admiration for the Garcia/Hunter songwriting partnership, but even here the books approach their subject in dramatically different ways, Richardson's subtle, sensitive readings replaced with Kreutzmann's almost taunting bluntness: "I liked the Jerry Garcia songs the best. That should come as no surprise. Jerry Garcia's music with Robert Hunter's lyrics was the best of what we had to offer and getting to play those songs was the reward for being a good sport about the rest."

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While not introspective, Deal does feel honest; its directness produces genuinely moving moments, most often in relation to Garcia, of whom Kreutzmann was endlessly fond. Reflecting on the guitarist's heroin use, Kreutzmann admits that "there was a certain feeling toward the end, that Jerry was using the Grateful Dead to finance his drug habit. That's a sad thought." Throughout, one feels how unhappily the band wore the heavy blanket of fame, especially after their explosive late '80s success. Rather than take time off to clean up and rest, they soldiered on, not for the music, but to sustain the massive organization they'd created – "the beast had to be fed."

The beast didn't love being a beast. In 1988, fans who'd ordered tickets to the Dead's spring tour through the band's mail order operation were treated to a surprise when their envelopes arrived – a rare pronouncement from the group in the form of letter from Robert Hunter, in which he rejected, in the grand Grateful Dead tradition, almost every fan-projected narrative. "We are not a political, religious nor a grassroots movement," he wrote. "Not a counterculture, drug culture nor the latest big shakes snatch-and-run glamour act. We are a symbiotic fun machine designed to get 10,000 or more heads straight at a pop."

We're not, in other words, what you want us to be. But they somehow were – are – everything, to millions of fans around the world; that's the riddle of the Grateful Dead. Neither of these books, and very few of the long list of others that have come before, feels like it captures anything definitive. Even Kreutzmann seems to recognize that there's no one Grateful Dead, that we all have our own. "It's funny," he writes. "All these things are part of the Grateful Dead story, sure. But they're not necessarily my story."

Which leaves the reader in something of a quandary. When no approach to telling the story quite works, what do you do? I'd suggest using your ears instead of your eyes. As Richardson notes in No SimpleHighway, "between the Dead's live recordings and those of the tapers, more than two thousand Dead concerts were eventually recorded…the Dead put more music into circulation than any performing group in history." I'm stuck these days on 6/9/77, which you can stream for free at archive.org. As Garcia sings during that night's enormous version of Franklin's Tower, one of the finest versions of one of the band's most ebullient jams, "If you get confused, just listen to the music play."

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